Catalytic Asymmetric Claisen Rearrangement of Enolphosphonates: Construction of Vicinal Tertiary and All-Carbon Quaternary Centers

A copper‐catalyzed enantioselective Claisen rearrangement of easily accessible enolphosphonates using the commercially available PhBOX as the chiral ligand was developed. A wide range of rearrangement products with contiguous tertiary and all‐carbon quaternary centers were obtained in excellent yiel...

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Published inAngewandte Chemie International Edition Vol. 51; no. 33; pp. 8264 - 8267
Main Authors Tan, Jiajing, Cheon, Cheol-Hong, Yamamoto, Hisashi
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 13.08.2012
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Accessibility
asymmetric catalysis
Asymmetry
BOX ligands
Catalysis
Catalysts
Chemistry
Chemistry, Multidisciplinary
Claisen rearrangement
Construction
copper
Functional groups
Ligands
Molecular Structure
Organophosphonates - chemical synthesis
Organophosphonates - chemistry
Physical Sciences
quaternary carbon centers
Science & Technology
Stereoisomerism
Stereoselectivity
BOX ligands
DIELS-ALDER REACTIONS
FRIEDEL-CRAFTS ALKYLATIONS
asymmetric catalysis
ENANTIOSELECTIVE CONSTRUCTION
ENE REACTIONS
MICHAEL REACTIONS
BIS(OXAZOLINE) COPPER(II) COMPLEXES
VINYL ETHERS
ALPHA,ALPHA-DISUBSTITUTED ALDEHYDES
quaternary carbon centers
copper
Claisen rearrangement
TBOX CHROMIUM COMPLEX
CONJUGATE ADDITION
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Summary:A copper‐catalyzed enantioselective Claisen rearrangement of easily accessible enolphosphonates using the commercially available PhBOX as the chiral ligand was developed. A wide range of rearrangement products with contiguous tertiary and all‐carbon quaternary centers were obtained in excellent yields and stereoselectivities. The α‐ketophosphonate substituent in the products could be easily transformed into other functional groups.
Bibliography:NIH - No. P50 GM086 145-01
Support of this research was provided by the NSF (CHE-1049551) and NIH (P50 GM086 145-01). We thank Dr. Antoni Jurkiewicz for NMR, Dr. Ian M. Steele for X-ray analysis and Dr. Furong Sun (UIUC) for MS data. Dr. David Dickson is acknowledged for his original work for this project.
ArticleID:ANIE201203092
ark:/67375/WNG-5PJVNFW8-S
NSF - No. CHE-1049551
istex:7CA477DF446C4C5D92B41D4D16F00D9FAE6E8BF6
Support of this research was provided by the NSF (CHE‐1049551) and NIH (P50 GM086 145‐01). We thank Dr. Antoni Jurkiewicz for NMR, Dr. Ian M. Steele for X‐ray analysis and Dr. Furong Sun (UIUC) for MS data. Dr. David Dickson is acknowledged for his original work for this project.
NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201203092